2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic Dianhydride TCI D4339

Chemical Identity

CAS No.: 83204-68-6
Formula: C14H2Br2O6
Molecular weight: 425.97 g/mol
Purity: >98.0%(HPLC)(T)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 2,9-dibromo-6,13-dioxatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8,10,15-pentaene-5,7,12,14-tetrone
SMILES: C1=C2C3=C4C(=CC(=C3C(=O)OC2=O)Br)C(=O)OC(=O)C4=C1Br
InChIKey: FEDCHNPLDKDTNS-UHFFFAOYSA-N
MDL: MDL00406909
PubChem: CID 11974609

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TCI D4339 2,6-Dibromonaphthalene-1,4,5,8-tetracarboxylic Dianhydride is a material building block designed for organic semiconductor research. Its molecule consists of a naphthalene core carrying two anhydride groups at both ends together with two bromine atoms at core positions. In the laboratory, this compound serves as a primary precursor for the preparation of naphthalene diimides, a family of dyes and semiconductors of considerable importance in the development of organic transistors, organic solar cells, and charge-storage materials. Reaction with primary amines converts the anhydride groups into imides directly and efficiently.

The principal advantage of this compound is the presence of the two bromine atoms on the naphthalene core. This core substitution gives researchers additional control over the electronic properties of the resulting material, because the bromine atoms can be replaced through cross-coupling reactions, nucleophilic aromatic substitution, or reactions with sulfur and nitrogen nucleophiles in order to install donor or acceptor groups. In this way, orbital energy levels, band gap, solubility, and colour of the material can be tuned systematically. The naphthalene diimide core itself is known to be electron-poor, which makes it one of the reference scaffolds for n-type organic semiconductor design.

In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic electronics, functional dyes, and macromolecular materials. It is generally handled at the synthesis bench in small research-scale quantities, where the dianhydride is condensed with selected amines and the brominated positions are subsequently functionalised. Supplied under the TCI brand with catalogue code D4339, it fits synthesis programmes that require a defined, reproducible starting material for building larger semiconductor structures.

Naphthalene diimide synthesis: the two anhydride groups react directly and efficiently with primary amines, giving laboratories a straightforward route to imide products without additional activation chemistry.
Organic transistor material development: the electron-poor naphthalene diimide core derived from this compound is a reference scaffold for designing n-type organic semiconductors used in transistor research.
Organic solar cell research: derivatives prepared from this dianhydride belong to the dye and semiconductor family applied in the development of organic photovoltaic devices and acceptor materials.
Cross-coupling and substitution chemistry: the two core bromine atoms can be replaced by cross-coupling, nucleophilic aromatic substitution, or reaction with sulfur and nitrogen nucleophiles to attach donor or acceptor groups.
Electronic property tuning studies: core substitution through the bromine positions allows researchers to adjust orbital energy levels, band gap, solubility, and colour of the resulting material systematically.

Brand	TCI, catalogue code D4339
CAS number	83204-68-6
Molecular formula	—
Purity	—
Category	Materials Science > Material Building Blocks > Polymer/Macromolecule Semiconductor Building Blocks
Pack sizes	research-scale packaging as offered by TCI for this catalogue code; please confirm the available size when ordering
Physical form	—
Storage	keep in the original tightly closed container as indicated on the manufacturer's label

Chemical class: brominated naphthalene tetracarboxylic dianhydride, precursor to naphthalene diimides

Store the container tightly closed in a cool, dry, and well-ventilated area, away from moisture, since anhydride functional groups are sensitive to hydrolysis. Keep the material in its original manufacturer container or in a chemically compatible, clearly labelled alternative, and reseal immediately after weighing. Handle in a fume hood using gloves, safety glasses, and a laboratory coat, and avoid generating or inhaling dust during transfer. Keep the compound separate from amines and other reactive nucleophiles except during intended synthesis steps. Always consult the manufacturer's safety data sheet before use, and follow institutional procedures for waste collection and disposal.

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